Verdict: For most small businesses, ChatGPT Plus ($20/user/mo) is the best standalone AI assistant because it has the broadest app ecosystem, image generation, and easy sharing. If your team already uses Microsoft 365, Microsoft 365 Copilot ($30/user/mo) is the better fit. Choose Claude Pro for long-form writing and coding, and Google AI Pro / Gemini for Workspace if you live in Gmail, Docs, and Sheets.
Last verified: 2026-06-14 · Pricing/limits are volatile — confirm before you buy.
At-a-glance comparison
| Assistant | Price (confirmed) | Best for | Key limit |
|---|---|---|---|
| ChatGPT Plus | $20/user/mo confirmed | General business tasks, marketing copy, quick automations | Output needs editing; no native work-data grounding |
| Claude Pro | $20/mo (or $17/mo annual) confirmed | Long writing, coding, careful reasoning | Smaller third-party app ecosystem than ChatGPT |
| Google AI Pro | ~$19.99/mo reported | Gmail, Docs, Sheets users; low price | Workspace integration quality varies by app |
| Microsoft 365 Copilot | $30/user/mo confirmed | Teams already on Word, Excel, Outlook, Teams | Requires qualifying Microsoft 365 base plan |
What an AI assistant does for a small business
An AI assistant is your always-available helper for drafting emails, summarizing meetings, researching, writing content, analyzing spreadsheets, and answering questions. The right one becomes the first place your team goes when they are stuck.
ChatGPT Plus — best overall for most small businesses
- Price: $20/user/month, confirmed by OpenAI in June 2026.
- Models: GPT-5.5 family on Plus; GPT-5.5 Pro on higher tiers.
- Why it wins: Largest selection of integrations and custom GPTs, built-in image generation (DALL-E), voice mode, and decent data analysis.
- Where it falls short: Responses can be generic without good prompting; it does not automatically know your company files unless you upload them.
- Source: openai.com/chatgpt/pricing
Best small-business use cases
- Drafting blog posts, email newsletters, and ad copy
- Turning a spreadsheet into insights
- Generating social images and simple graphics
- Building repeatable prompts for common tasks
Claude Pro — best for writing, coding, and reasoning
- Price: $20/month, or $17/month with annual billing, confirmed by Anthropic in June 2026.
- Models: Sonnet 4.6 default; Opus 4.8 and others available.
- Why it wins: Exceptional at long-context tasks, nuanced reasoning, coding with Claude Code, and producing natural-sounding prose.
- Where it falls short: Smaller app marketplace; less multimedia/image capability than ChatGPT.
- Source: claude.com/pricing
Best small-business use cases
- Writing detailed proposals, reports, and white papers
- Coding or debugging scripts and small automations
- Turning scattered notes into structured documents
Google AI Pro / Gemini for Workspace — best for Google-first teams
- Price: Google AI Pro reported at ~$19.99/month; Gemini for Workspace Business reported at ~$20/user/month.
- Why it wins: Lives inside Gmail, Docs, Sheets, Meet, and Drive. Useful for people who already organize work in Google apps.
- Where it falls short: Mixed reviews on quality in Gmail and Meet; requires a qualifying Workspace plan for business features.
- Source: Secondary reports from Google I/O 2026; verify at one.google.com/gemini
Best small-business use cases
- Summarizing long email threads
- Generating first drafts in Google Docs
- Creating slides and spreadsheet formulas
Microsoft 365 Copilot — best for Microsoft-first teams
- Price: $30/user/month, confirmed by Microsoft in June 2026.
- Why it wins: Grounded in your work data (emails, files, meetings) through Microsoft Graph; works inside Word, Excel, PowerPoint, Outlook, and Teams.
- Where it falls short: Requires a qualifying Microsoft 365 business plan; steepest per-user cost on this list.
- Source: microsoft.com/copilot/pricing
Best small-business use cases
- Summarizing Teams meetings and generating follow-ups
- Drafting emails and documents grounded in company context
- Building Excel models and PowerPoint decks from prompts
How to choose
| If you... | Choose |
|---|---|
| Want one AI tool for many jobs | ChatGPT Plus |
| Write long content or code | Claude Pro |
| Live in Gmail/Docs/Sheets | Google AI Pro / Gemini for Workspace |
| Use Microsoft 365 for everything | Microsoft 365 Copilot |
| Have a tight budget | ChatGPT Go ($8/mo) or Google AI Plus ($7.99/mo reported) |
What this means for you
Most small businesses should start with ChatGPT Plus. It is the safest default and covers the widest range of everyday tasks. Only upgrade to Copilot if your business is already committed to Microsoft 365 and the $30/user/month cost is justified by time savings.
Related reading
- ChatGPT losing its majority in the 2026 AI assistant race
- AI research assistant update for small teams
- Best AI Customer-Service Tools for Small Business in 2026
FAQ
Can one AI assistant replace multiple tools? Partially. A strong assistant reduces the need for separate writing, research, and basic analysis tools, but specialized software (bookkeeping, CRM, project management) still wins for its specific job.
Is my business data safe with these assistants? Paid business tiers generally promise not to train on your data, but policies differ. Review each vendor’s business/enterprise data policy before uploading sensitive files.
Should I pay per user or share one account? Sharing one account violates most terms of service and breaks security. Budget for one seat per person who will use it regularly.
Do these assistants work on mobile? Yes. ChatGPT, Claude, Gemini, and Microsoft Copilot all have mobile apps or mobile web access.
Where does this fit in the broader AI-for-small-business hub? See AI for Small Business: The Complete Guide and our job-by-job tool guide Best AI Tools for Small Business in 2026.
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